Esc Hero #23: Leaving the law to start up greentomato

It is a great pleasure to introduce Tom Pakenham, one half of greentomato – “everyday life made greener”

Tom left his city law firm to start greentomatocars so he is a true Esc Hero!

Have a read below to learn about how he transitioned out of a mainstream corporate job to do his own thing.

1. What are you currently doing?

Right now I’m working on the launch of the next big greentomato business – greentomatoenergy. This is a renewable energy and low carbon building business which officially kicks off in January. We’re also continuing to grow the greentomatocars business which now has over 100 cars, and working on some exciting taxi-related business ideas. greentomatocars – London’s green taxi company – is the business I left the city to set up.

2. What did you do before this and how long did you do it for?

On leaving university, I worked as a runner and assistant director in the film industry. After realising that wasn’t the thing for me, I went to law school (BPP) and then on to Slaughter and May, where I qualified as a solicitor in an IP and M&A department. I was at Slaughter and May for 2½ years.

3. How long have you dreamt of doing this?

I have always dreamt of setting up my own business, it was just about coming up with the right idea. One early idea was an anger-management booth where people in the city could pay a fiver in their lunch break (if they got one) to smash up some crockery, or statue in the shape of their boss. I think Escape the City is a much healthier outlet for that kind of frustration!

Over time it became clear that the business idea would be in the environmental sector. Business ideas generally seem to arise in response to a perceived need, and the environment seemed to me to be ripe with needs. So it was a question of picking the right one.

4. What was the Moment of Truth?

Well, the dream had been crystallizing for ages, but I do remember clearly the moment I decided to go for it. I was having a lie-in one Saturday morning breathing the weekly sigh of relief that it wasn’t a work day, and I realised there was never going to be a better time to make it happen. It just kind of clicked.

5. From a practical perspective, how did you plan for it?

I did plenty of work researching the area before handing in my notice, enough to know that transferring into the cleantech space stood a good chance of being a productive and satisfying move. After leaving Slaughter and May, I spent a year researching the enormously complex range of subjects associated with the environment at the same time as learning more about the private hire industry.

My private hire research included driving for Addison Lee and another cab company – this was a fascinating and invaluable experience. A minimum level of industry understanding is essential when launching a new business.

Once I had decided that I would definitely like to give the car business a go, I asked my business partner – Jonny Goldstone – to come on board. His input added hugely to the momentum and from that point there was no looking back. But there was always the element of risk, which I didn’t have a problem with.

6. How did you fund it?

I was lucky enough to own my own flat, so to cover my living costs while I was in the planning stage, I let it out and moved back home with my mum. Then, when I finally decided to launch the business, I sold my flat which raised most of the funds we needed to start a pilot business with a fleet of 4 cars. The rest came from my business partner and my mum.

Later when it came to a crucial stage of growing the fleet, we sought investment from a third party investor. We had quite a bit of interest at this stage and were able to choose our investor who is a real support of the overarching vision of greentomato, which is exactly what a young business needs.

7. What was the hardest thing about making this happen?

I think the obvious answer is dealing with the gut-wrenching fear of failure and losing everything and everyone laughing at you, and that definitely played a part. But actually something I found very difficult indeed was working on my own in the initial planning stages. Having a business partner is a significant advantage.

8. What has been the best thing about having made this happen?

The opportunities that it presents for the future. When you have made the leap into the unknown once, you get a taste for it.

9. What advice would you give to other people?

Plan as carefully as you can, but don’t expect to have all the answers. Also, check that you’re okay with risk – being your own boss is all about taking a risk, so if that gives you nightmares, it’s probably better not to subject yourself to it.

10. What resources did you find really useful?

On the subject of actually leaving a City career, there was no single resource that was all that useful (which is why Escape the City is such a good idea). Talking to people you trust is important, but don’t expect them all to support you. And if they don’t, think about their motives for why they are not supporting you.

Ultimately, you know inside whether you are doing the right thing and you will make the right decision accordingly.

On the subject of the environment, it is such a big area that you need to read absolutely everything and talk to absolutely everyone and never think that you know anything.

11. What else?

Be prepared for a long hard slog and lots of sleepless nights. Don’t be afraid of failure, because although it’s good to have a healthy dose of fear, too much will blunt your creativity and negatively affect the impact you have on those around you; at work and at home.

Finally, I have found that a strong belief set about the environment, and passion for it, have helped me through the more mundane and difficult aspects of the work that I do.

If you have a passion, with a bit of planning everything else will follow.

About Escape the City

Frustrated by climbing the corporate ladder, we decided to build a community to help people build meaningful careers doing work that matters – to them and to the world. We help talented people find fulfilling work by making big career changes, building businesses, & going on big adventures. We’d love you to come with us on this journey.